EP2477984A4 - A method for the n-demethylation of n-methyl heterocycles - Google Patents

A method for the n-demethylation of n-methyl heterocycles

Info

Publication number
EP2477984A4
EP2477984A4 EP10816472.4A EP10816472A EP2477984A4 EP 2477984 A4 EP2477984 A4 EP 2477984A4 EP 10816472 A EP10816472 A EP 10816472A EP 2477984 A4 EP2477984 A4 EP 2477984A4
Authority
EP
European Patent Office
Prior art keywords
demethylation
methyl heterocycles
heterocycles
methyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP10816472.4A
Other languages
German (de)
French (fr)
Other versions
EP2477984B1 (en
EP2477984A1 (en
Inventor
Peter John Scammells
Gaik Orbell
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Monash University
Original Assignee
Monash University
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from AU2009904493A external-priority patent/AU2009904493A0/en
Application filed by Monash University filed Critical Monash University
Publication of EP2477984A1 publication Critical patent/EP2477984A1/en
Publication of EP2477984A4 publication Critical patent/EP2477984A4/en
Application granted granted Critical
Publication of EP2477984B1 publication Critical patent/EP2477984B1/en
Not-in-force legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D489/00—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula:
    • C07D489/06—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula: with a hetero atom directly attached in position 14
    • C07D489/08—Oxygen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B37/00—Reactions without formation or introduction of functional groups containing hetero atoms, involving either the formation of a carbon-to-carbon bond between two carbon atoms not directly linked already or the disconnection of two directly linked carbon atoms
    • C07B37/06—Decomposition, e.g. elimination of carbon dioxide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
    • C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
    • C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
    • C07D451/06—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
    • C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
    • C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
    • C07D451/06—Oxygen atoms
    • C07D451/10—Oxygen atoms acylated by aliphatic or araliphatic carboxylic acids, e.g. atropine, scopolamine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D489/00—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula:
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D489/00—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula:
    • C07D489/02—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula: with oxygen atoms attached in positions 3 and 6, e.g. morphine, morphinone

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
EP10816472.4A 2009-09-16 2010-09-16 A method for the n-demethylation of n-methyl heterocycles Not-in-force EP2477984B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
AU2009904493A AU2009904493A0 (en) 2009-09-16 A method for the N-demethylation of N-methyl heterocycles
PCT/AU2010/001204 WO2011032214A1 (en) 2009-09-16 2010-09-16 A method for the n-demethylation of n-methyl heterocycles

Publications (3)

Publication Number Publication Date
EP2477984A1 EP2477984A1 (en) 2012-07-25
EP2477984A4 true EP2477984A4 (en) 2013-04-10
EP2477984B1 EP2477984B1 (en) 2016-08-03

Family

ID=43757944

Family Applications (1)

Application Number Title Priority Date Filing Date
EP10816472.4A Not-in-force EP2477984B1 (en) 2009-09-16 2010-09-16 A method for the n-demethylation of n-methyl heterocycles

Country Status (3)

Country Link
US (1) US9073934B2 (en)
EP (1) EP2477984B1 (en)
WO (1) WO2011032214A1 (en)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8962841B2 (en) 2007-06-29 2015-02-24 Brock University Methods for one-pot N-demethylation/N-functionalization of morphine and tropane alkaloids
ES2613403T3 (en) * 2011-05-06 2017-05-24 Brock University Process of preparing morphine analogues by metal catalyzed N-demethylation / functionalization and intramolecular group transfer
AR091779A1 (en) 2012-07-16 2015-02-25 Rhodes Technologies PROCEDURE FOR IMPROVED OPIOID SYNTHESIS
SG11201407988UA (en) 2012-07-16 2015-01-29 Rhodes Technologies Process for improved opioid synthesis
CN103044327B (en) * 2013-01-07 2014-12-17 苏州立新制药有限公司 Preparation method of dextromethorphan
CN103073494B (en) * 2013-02-04 2015-10-07 苏州立新制药有限公司 The preparation method that ent-3-methoxyl group is muttered
CN103073495B (en) * 2013-02-06 2015-08-05 苏州立新制药有限公司 The preparation method that a kind of ent-3-methoxyl group is muttered
CN103254131A (en) * 2013-04-23 2013-08-21 苏州谷力生物科技有限公司 Refining technology for dextromethorphan bulk medicine
GB201313915D0 (en) 2013-08-02 2013-09-18 Johnson Matthey Plc Process
MX2016009125A (en) 2014-01-15 2017-02-02 Rhodes Tech Process for improved oxymorphone synthesis.
MX2016009300A (en) 2014-01-15 2017-04-13 Rhodes Tech Process for improved oxycodone synthesis.
US20160340362A1 (en) * 2015-05-20 2016-11-24 Noramco, Inc. Process For The Preparation Of Oxymorphone Freebase
WO2017185004A1 (en) * 2016-04-22 2017-10-26 Noramco, Inc. Processes and oxazolidine-containing intermediates for the preparation of morphine analogs and derivatives
US10626120B2 (en) 2016-04-22 2020-04-21 Noramco, Llc N-demethylation of morphinan alkaloids
EP3570842A1 (en) 2017-01-19 2019-11-27 Donald Danforth Plant Science Center Morphinan n-demethylase isolated from themethylobacterium
US11247999B1 (en) * 2021-07-02 2022-02-15 Joseph DeGraw Facile conversion of morphine to normorphine

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002016367A1 (en) * 2000-08-25 2002-02-28 Glaxo Wellcome Australia Ltd Chemical methods
EP2062897A1 (en) * 2007-11-26 2009-05-27 Siegfried Ltd. Demethylation of 14-hydroxy substituted alkaloid derivatives

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5270317A (en) * 1990-03-20 1993-12-14 Elf Sanofi N-substituted heterocyclic derivatives, their preparation and the pharmaceutical compositions in which they are present
US7935820B2 (en) 2007-06-29 2011-05-03 Brock University Methods for N-demethylation of morphine and tropane alkaloids

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002016367A1 (en) * 2000-08-25 2002-02-28 Glaxo Wellcome Australia Ltd Chemical methods
EP2062897A1 (en) * 2007-11-26 2009-05-27 Siegfried Ltd. Demethylation of 14-hydroxy substituted alkaloid derivatives

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of WO2011032214A1 *

Also Published As

Publication number Publication date
US20120226043A1 (en) 2012-09-06
EP2477984B1 (en) 2016-08-03
US9073934B2 (en) 2015-07-07
EP2477984A1 (en) 2012-07-25
WO2011032214A1 (en) 2011-03-24
AU2010295236A1 (en) 2012-04-05

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